Keith Rabois on Trump Vs Kamala, Founder Mode & Mastering time like Elon Musk

So if something feels comfortable, it's too easy and stop doing it and find something that makes you want to throw up that you feel that. Oh my God, this is so difficult.

Keith Raboy, one of the world's most successful technology entrepreneurs, investors, and member of the legendary PayPal mafia. How does Elon Musk do so much with the same 24 hours as the rest of us?

Gas expands the size of the container, so if you give people a quarter, it'll take a quarter. Tell them a week, it'll take a week. So you want to constantly compress the container size.

He's a managing director at Khosla Ventures, CEO at Open Store, and former executive at PayPal, LinkedIn and Square.

You're basically constructing an engine. You're actually duct taping that engine together every day, every week, every quarter, every year you replace some of that duct tape with metal. Constantly be turning duct tape and heroic effort into metal.

He successfully founded and invested in over $20 billion plus companies including Open Door, YouTube and Airbnb. Where are you leaning on the political election?

And why is there a difference between a close election and a volatile election? This election is not going to be. If no black swan occurs, Donald Trump will be the 47th president of the United States. There is good and evil, and he's on the right side. The other choice is on the wrong side of every foreign policy question for the last 50 years.

What goes into living a world class life?

Do something worth writing about or write something worth reading.

If you were to take away all of your accomplishments underneath all that, who is Kiefer Boy? First thing I want to talk about is founder mode. Why do you think this is going so viral and what is your take on founder mode?

Ultimately, when you're the CEO, you're accountable and responsible for everything and you can't really delegate things without abdicating. There's a set of principles about what does that actually mean? How do you double click on things? How much responsibility do you have for any decision? But I think a lot of people have learned sort of this MBA speak. Brian went through this evolution of listening to conventional general management MBA stuff and really layered on one or two levels of bureaucracy at Airbnb and was basically advised not to dig into the details and then realized that he wasn't really building the company he wanted to build. He wasn't achieving the goals that he set out to. The ambition, the market cap even. And so he ripped the whole thing apart like late December 19th. Rebuilt the company from the ground up to be the company he wanted to build, which is where the executives who run things are masters of the details. This is actually what we built at PayPal. So at PayPal we never promoted anybody based upon their management skill. We promoted everybody based upon their craft. So if you wanted to be running the design team, you had to be the best designer. If you wanted to run the engineering team, you had to be the best engineer. If you wanted to run product, you had to be the best product person, or a CFO was the best finance person. And so we always had that philosophy at PayPal. Maybe that's why PayPal thrived and maybe why, you know, my friends and colleagues went on to do very interesting things, is they basically brought with them many of those tenants. So Brian reinvented it and repopularized ideas that are pretty old school actually. So it's the antithesis of hiring a general manager, someone whose expertise is really, really at managing versus someone whose expertise is actually at building. Because I think when you hire for founder mode, you're looking for different people. It doesn't mean you don't hire anybody. Obviously you need to scale an organization. Brian probably has thousands of people. Doordash has thousands of people. You can't do everything the same way. You can't run things the same way. When you had 10 people or 20 people, you do need to hire, but you need to look for different traits, different skills.

I like that because yeah, a lot of the companies got very bloated with these middle managers that actually had no domain, expertise or craft in that space. And then they're disseminating terrible information down the rest of the company.

Well, as you've seen for Elon, elon ripped out 80% of the employees at AX&X is thriving. Yeah, I think Elon's always been in founder mode. He's an illustration. I think Apple basically has been in founder mode through most of its history. Basically at Apple you get promoted by mastering something, not by being a generalist. There's people you meet and you've probably recruited people out of Apple that have done the same thing basically for 15 years. But they are the world class expert at X and that's what they do. And Apple collates and collects a bunch of people who are literally the best in the world at 26 different things and mixes them together. That's a much better model.

What do you think of like a lot of times, like the first AE in a company, the best salesperson ends up totally flopping as the VP of sales. Right. They can't Elastically scale into leadership. And so sometimes the most talented IC does not become the best leader and they fail in that position.

I actually think they should be able to. Sometimes it's mentoring, pairing them with the right person, giving them the right feedback. But at least if you promote that person, you're not going to demoralize your team because everybody knows that they were the best salesperson. They put that quota up, Everybody knows that they were kicking ass and, you know, taking names. And so the rest of the teams are going to look up to that person because that person can actually deliver the goods. They may have to learn how to coach and mentor other people, but you have enthusiasm, energy from the rank and file. You bring in someone who's never hit a quota, never proven that they can sell product X and you're like, oh, you're your new manager. Sometimes people are like, who the hell are you? And it's a very valid critique.

Yes. Because you talk a lot about writing versus editing. Right. Like, I think you learned that from Jack Dorsey.

I did.

Right. And so as in founder mode, you want to be in the details of across as much scope as possible, but having other people writing most of the things and you're editing, but you're still in the trenches. There are there things that you believe that founders should never delegate.

So I have a framework in my how to operate lecture that I taught in 2014 for YC, which is available online. I have a grid, a two by two matrix of when you should delegate and when you should take personal responsibility. And the grid roughly has two dimensions, which is basically your level of conviction in knowledge or expertise. And then secondly the importance like high upside, high downside, so asymmetry of result. When you're in box one, high conviction, high asymmetry, you have to make that decision every single time. And you're in the last quadrant, the easy quadrant. Low impact, low conviction. You should delegate that because people will surprise you. It's a good way to test how strong is your team. You let them make decisions and you watch and you watch and learn. And if sometimes people surprise you and they're like, wow, holy cow, this person's amazing, they made decisions that I wouldn't have made, but they were better. And so then you promote those people. You expand the scope and complexity of what those people are responsible for. The quadrants in between, the other two quadrants are a little bit more tricky and complicated. And I talk about how do you make those decisions? If you go back to the history of Silicon Valley, Andy Grove, who is one of the most important people in the history of Silicon Valley. I put him on my hall of fame last time in the top five of all time. Wrote a book called high output management 1982. It's still the bible on how to run a high tech, high growth startup. And basically what he teaches is a concept of task relevant maturity which is you're going to inspect and probe based upon your leader's experience with a similar curriculum. So when someone's trying to do something for the first time, you may inspect their work product every single day. When they've proven that they can do something like that successfully, both in your company, maybe even outside your company, you may inspect every month. So it varies by person. So there's no right formula. It's by the specific person, their expertise and the importance to the company.

So that's why Brian Chesky was like I spent more time than most would have said I should have on all the product memos, the product marketing, getting every detail right. So eventually now the foundation was built so well and people know how I think and what my standard is. So I can now I can pull back more.

Another way to reframe this is when I was interviewing for Square to work for Jack. He obviously conducted reference checks. We didn't know each other very well before I joined and he got, you know, somewhat disconnected feedback. Some people said I was a micromanager, some people said I wasn't and I delegated a lot of and actually at first I thought that was a criticism but actually I realized that it's exactly right. You want to micromanage some people in some verticals, some domains product, let's say if you're Brian, especially because you're world class at it. And then there's some areas where you want to give slack either because the leader has proven so. For example, at Open Store we're building out a fulfillment center, our own internal fulfillment center. The team that's building this has done this for 25 years, starting at Amazon five times successfully. There's no way I need to double click every day on how this fulfillment center is going to operate. It's going to be under budget, on time and it's going to work perfectly. So I just delegate a lot of the fulfillment center. I might ask a question or two per quarter, but that's it. Because they are the best in the world at building one.

When we talk about scaling world class companies, I like how you talk about you need to build an idiot proof company, right? Because eventually it will be run by eventually at some Google today. So when you think about building an idiot proof company, you're thinking about systems frameworks, like what goes into that for you.

You're basically constructing an engine and it's a system. The engine just runs now at first you're actually duct taping that engine together. I have a kind of cool image in my lecture about it. You're holding it together through heroic effort. And then every day, every week, every quarter, every year, you want to build some of that, you want to replace some of that duct tape with metal. And the metal's permanent and may have a decade before it starts to rot. And that's basically what you want do is constantly be turning duct tape and heroic effort into metal.

I love that. That's so good you talk about building these frameworks. So like this is very relevant for me right now too because as you scale, you want to be involved in everything. You want to make sure decisions are being made at the highest level of acumen possible. But in order to scale an organization, you have to have frameworks for decision making so that you can trust that decisions are being made effectively by other people. And you have to start building SOPs and you know, and doing all that kind of stuff. Like how do you build a decision framework so that you can disseminate decisions across the organization without having to be bottlenecked by the CEO?

I think ultimately you appoint DRIS is the best model which is directly responsible individual. It's borrowed from Apple intentionally. And then there's a point person who's responsible for marshaling all the information, all the trade offs and presenting it. The person may not decide, but the person is responsible for doing all the pre work, then you can as CEO if you want to decide, you can in a very efficient way. Maybe a 10 minute, maybe less, maybe a half hour, maybe an hour. You can actually have all the context because someone else has exhaustively researched the trade offs and presents them in a succinct, powerful way. And you can immediately dial into what are the key variables and what are the key trade offs. One of the things that CEOs are typically really good at is understanding trade offs because they have context. And ideally you push the context down as Netflix teaches you want everybody to have as much context as possible. But knowing where you're going and what those trade offs are in terms of going to Mars is something the CEO usually has the best visibility into. If you synthesize everything, distill everything, and research everything in advance, those meetings can be incredibly productive in there. Whether you call them reviews, whether you call them quarterly business reviews, it doesn't really matter. It's just someone's responsible for marshaling everything. So you can immediately digest, dive in and decide. And if the information is not presented correctly, succinctly, exhaustively, it just basically makes the entire organization dysfunctional.

You're flying blind.

Yeah. Or like, you know, it's inefficient because if you have to go back and say, hey, what about this, what about that? It's actually one of the things that ventures, I would say, not really good at training people to be CEOs. But one thing that is good is you have to learn new things really fast. So someone walks in at a pitch meeting and they're usually talking to me about something I know nothing about. And within X minutes I need to get very sharp, very fast. In executive, it's somewhat similar is like you may have more time to study and you may have more depth, but fundamentally you're always being presented with novel ideas, novel problems, newfangled solutions and the skill of learning curve. The ability to absorb new information really fast and dive in and get to a comfort level is a pretty transferable skill of leading executive.

How do you think through SOPs? Because at the end of it, if we're building an engine, we want a well documented like oiled machine so someone can come into a new department. They know exactly what the standard of greatness, the workflows look like. Who is responsible for creating the SOPs for each department?

Someone else should definitely be doing the writing. The CEO is responsible for consistent, uniform voice in editing up to a certain quality, just like an editor of a book. And so we're editor of a newspaper or editor of a magazine. Basically you want one voice, one strategy and one benchmark of quality. And that's an editorial role, that's not the writing role. You really, a CEO should very rarely be writing.

Do you create like an SOP for the SOP? Then like here's the structure.

Some CEOs, do they have like a style guide or you know, here's the framework for how to think about it. In venture we do, let's say a kv, we think of investment decisions in terms of three key questions. Like what are the key questions? There's usually three. And then we want to get as smart detail oriented as we can on just those topics and generally everything else rounds to not that important. So isolating the key questions, identifying them correctly, and then getting as insightful as possible as fast as possible on those three questions. So we have a formula at KV that we use and we really want our email memos to conform to that. And we really teach that to up and coming colleagues.

Yeah.

So any company maybe has a paradigm of what's the best possible way to tee up decisions.

That's interesting. So I'm curious for you, for founders that are looking to build their exec teams, what do you think? This might differ per company, but what do you think are the three most important executive hires a CEO has to get? Right.

First of all, every CEO has different strengths and different complementary needs.

Yes.

So, you know, I as a CEO have certain strengths and certain weaknesses. Brian may have different strengths and different weaknesses. And you know, Patrick Carlson may have a different set partially. You're building a baseball or basketball team around. You have a superstar. The CEO is a super, you know, superstar player. How you build a team may vary. Do you have a point guard superstar? Do you have a shooting guard superstar? Do you have a power forward or center superstar? So you're building definitely differently. Secondly, unlike basketball, you're competing in different markets. So competing SpaceX would be a different problem set than competing with Airbnb, than competing with stripe. And so partially where you want to compete, what dimension you're going to compete on may vary by market. And then how do you compete? So let's say Brian competes on the basis of design. So in design, competitive land, like a square, we competed on the basis of design, actually, and underwriting, but design too. If you're going to compete on a dimension, you need world class talent in that dimension, period, Full stop. There are other parts of an organization that are not your competitive wedge and you may hire differently in those areas. So you need more asymmetry of upside in the wedge and less asymmetry of upside, perhaps in other areas versus competence, proven confidence, less asymmetry of downside.

You mentioned at the beginning of the conversation that for founder mode companies, which we now I think widely understand are the best run companies that you, you tend to hire for a little bit different skill sets and traits. Can you give us, I know you're doing a speech on this on Thursday. Can you give us a preview? What are the traits?

One is just pure depth of craft, mastery of a topic. Like, you know, you do executive recruiting. Basically there's this T stop kind of version. So strong depth and then horizontal skill. Yeah, that's what we're looking for. Secondly is comfort level with the CEO owning the company. So some executives are like, hey, what are my goals? And you know, measure me at the end of the month or quarter and please don't interfere in the middle. In founder mode, the CEO is probably going to ask you questions all the time and do skip level meetings with your colleagues. And there are some executives who've been trained to be threatened by that and there's some executives who love it. So in a well run, high growth founder mode company, you might only hire 30% external hires. In a more traditionally run MBA driven company, you might hire 70, 80% external hires. So the mix of internal promotions versus external hires is very, very different. There's a ratio, it's never 100 or zero, but each, each company is its own cocktail brew of a mix. And you want to be somewhat conscious of am I trying to do 70% internal promotions? And I'd run the company differently if I were and I'd hire and I'd give you instructions as an executive recruiter differently versus if I was trying to get 70% of my executives from the world.

That's a really good distinction. What do you think? Because you've hired so many executives in your career, what do you think are the most common mistakes that founders make when they're hiring their executive?

Not really understanding what they need. So are you aiming for upside, asymmetry of upside, value creation, innovation, or you're aiming for value protection? So some roles you really want experience when you're in value protection mode, like experience helps you when you're trying to preserve value. So typically, let's say a cfo, typically let's say a general counsel, you're paying them to avoid unnecessary mistakes, to see around corners. If you're trying to do something that nobody else on the planet has ever done, expertise is usually not your friend. There's a reason why no one else has ever done it. And hiring people who have learned all the quote unquote reasons why something's impossible doesn't really help you. So you're almost better off hiring someone with no experience but with unusual slope of learning and potential to solve an innovative dilemma innovation problem. And once you had traction, scale, value creation, then you want some executives to protect you and their experience can be more your friend.

Let's assume we have a great founder. We're in founder mode. We've got a great executive team now we need to manage that executive team effectively. I'm really curious to get your take on this because I think it's a. There's polarizing views in Silicon Valley on this. You see Jensen Huang and Nvidia, who has something like 50 direct reports.

I think it's 32 or something.

He's up and down. But let's just say it's, it's asymmetric. The typical is maybe six to eight. Yeah, right. Massive exec team. He does not hold formal one on ones. He holds group meetings. My friend Howard Lerman over here at Rome Yext, he absolutely hates one on ones. Other more traditionally trained people, like no one on ones are absolutely critical when you have that, like, what's, what's your take on the optimal org chart design? And like, should you have 30 direct reports and run it more horizontally? Should you have fewer and run one on ones, what's, what's your take?

Well, so the conventional wisdom is like call it five to nine one on ones. Andy Grove recommends like five to seven. That's like traditional. And then obviously Jensen runs really hot. 33 is like off the charts.

Yeah.

As an executive, when I was at Square, I used to get myself in trouble with my board. I'd run pretty hot, like with 11 or so direct reports. And the reason why I'd run pretty hot is a, I'm pretty good at context switching. So the better the CEOs content naturally at context switching, the more direct reports you can, you can, you know, successfully run with. Secondly, there are benefits to a horizontal organization. A flat organization is really effective if the CEO can context switch with, you know, with that ability where it's not normal. Most human beings are not excellent or not adaptive context switching. So it's the rare exception. I think it's better if you can run horizontally flat to avoid a mistake of promoting someone. So I actually learned from Peter thiel back at PayPal that you only really want to promote someone when there's a significant delta between that person's performance and the next best person. The bigger the delta, the easier it is to promote somebody. Otherwise you're better off as an executive leading an organization to leave things flat until the gap is just unmistakable. Then you can stitch things together. The other reason you stitch things together though is somewhat different than individual executives is if there's trade offs every day or every week pairing metrics that are in conflict, you don't want to really be making that decision as the CEO on a weekly, daily basis, maybe not even monthly. So let's say there's a tension between, in financial services, which obviously have spent 23 years working in, there's tensions often between growth and risk. I don't as CEO really want to be making that trade off decision every week. So ideally I could fuse the growth role leadership with the risk leadership because then that executive can run the optimization function most of the time. And I don't need to interject myself. So how much tie breaking you're doing between functions also dictates the proper organization chart. And then it's just the potential of people. You don't really want to suppress someone's growth. So if you have a high potential executive leading an organization and you have 11 direct reports, artificially suppressing that person's potential by stitching them together under someone, layering them isn't really effective. You're going to demoralize them. You're never going to see how much upside they really have. And so as long as you think someone has unbounded upside, I'd be very leery of suppressing their potential.

That's the barrels you talk about.

Yeah, it applies to executives too. If you have someone. Steve Jobs used to talk about dynamic ranges. So you know, he's talking about how dynamic ranges in normal world, like non tech world, you know, are kind of one and a half to one. And in tech they're like 10 to one between engineer and a really great engineer. Executives, the dynamic range might be 1 to 1,000, 1 to 100, really. And so when you have someone who has unbounded potential, until you know where that dynamic range sort of plateaus, you don't want to do anything to curtail it. Because like value creation is driven by outliers. Tech companies, venture returns, individuals within a company are the outliers that produce the results. And so you don't want to. It's like you have the next Steph Curry in basketball, you have the next Aaron Judge. You want to give them the ball.

It's so true. And there's, there's this kind of, this kind of idea like everyone's replaceable. And I think that is true 99.9% of the time. But there's some people that are just not replaceable.

No, CEOs are not replaceable. That's why founder mode, that's why, you know, we invest in founders who have unfair advantages versus the rest of the planet. That's my job as an investor. It's the only thing I really look at is, is this founder. We've talked about it previously. But does this founder have the potential to change an industry, transform an industry or the world from scratch? From a proverbial garage?

Yeah.

And normal people don't do that. Normal people don't become 10 time all stars in any sport. Normal people don't become president of the United States. Normal people don't become the next kygos. Like, you need some competitive advantage. That's very rare. And so that's what I'm looking for when I fund somebody. But it's also how you want to run a company.

Yes.

Can you find the people that have those traits and give them the maximum opportunity to flourish?

I'm so curious to get your take on motivation and its signal on success. There's so many different motivations founders have. Some of them just want to solve a problem that's personal to them. Some of them want to just create a masterpiece. They're more like artists. Some of them are driven by deep insecurities to be seen by the world and want to prove something to the world or prove something to themselves so they can finally feel adequate in this world. Right. There's so many different deep motivational drivers. Do you think that there's any one that's more correlated with success?

No, I think as long as you have one of them, actually, I do think you need some deep motivation. Building a company is incredibly lonely. It's incredibly draining, and it's not for everybody. Elon talks about chewing glass, you know, intentionally. That's what building company feels like. Sometimes per hour, sometimes per day, sometimes per week. But Jensen talks about how painful it is he has. You know, it's worth watching his speeches on the topic. And so because of the degree of difficulty and the degree of pain, self sacrifice that you're inflicting on yourself, I think you need some intrinsic motivation. But what powers you, I think can be different. Any one of those three or four examples all were because I've noticed just.

In my own evolution, I think when I was first starting, like, everyone told me I couldn't do it. And that motivated the hell out of me. I was like, I'm going to prove everyone wrong. Right. I just. And I wanted to get to a certain place of security financially. And then maybe a year and a half, two years ago, I was like, everything is great now. And like, I don't have the same motive. I can't. I can't take this company into its full fruition with the same fuel, like. And so for me, I was like, I want to be more of an artist. I want to create a masterpiece of greatness. The greatest company that ever existed in this space. And that became the new fuel. Do you feel like your fuel source changed at any point in your career? Was it pretty.

It's pretty similar. I think it's pretty intrinsic to me, but I see how it could evolve I think your example is a really good illustration, but I think you need the motivation internally, but you can tap in possibly to different motivations.

But you've had such a. Like you've had almost three decades of just an iconic run here. What keeps you fueled?

Well, I think I like to do the impossible. I really do like investing in people and ideas that, that other people think are ridiculous. So proving people wrong, kind of, if you have to simplify it, I think that is exciting to me. Finding ideas or people that everybody else thinks dismisses, basically, and empowering them one way or the other to succeed. So I like the challenge. I'm basically always looking for challenges. That's why athletically, I like challenges. Challenges have always propelled me probably since I was six years old.

Yeah, the upside of stress we talked about last time I've read that book, by the way, is freaking fantastic.

Yeah, highly recommend it.

I'm curious, you know, just in light of recent events. I saw Elon yesterday. I think in one week he's got like the robo taxi, he's got the, the, the starship test flight, he's got Optimus robot, all the president campaigning for president. He's at the next Trump rally. I mean, you know, this guy obviously seems to do superhuman things in parallel that most people could never even imagine doing with the same 24 hours as the rest of us. I'm really curious on your thesis, how does Elon Musk do so much with the same 24 hours as the rest of us?

What'd you do this week?

Yeah, what'd you do this week? I'm like, I didn't do shit.

Well, I mean, honestly, that's very insightful. Which is, if you approach every day and every week of your life with what you accomplished this week, I think that compounds. And very few people do that. So I think that's the number one ingredient. Second thing is, I think he's founder mode on Steroid. I should have pointed this out that he's built all of his companies in founder mode. So when he was taking over X, I kind of tweeted out this example I knew from SpaceX. Some friends of mine had been interns at SpaceX and I sort of warned the Twitter politically correct crowd that worked there that they were in for a rude awakening. And I gave this example of he once caught some interns in line waiting for a coffee at SpaceX. There was a line of interns piling up around their coffee machine, SpaceX. And he sent a memo to the company about it saying, wait, why are all the interns wasting all this time? If you think feel like you have nothing better to do than waiting in line, you know, you're at the wrong company. And by the way, I'm installing cameras to make sure that we don't have lines at the coffee shop. And so, you know, people, people went crazy on Twitter at the time because they're like, oh, my God, that's so evil. You know, how could you do that? Put aside whether, you know, companies should even have coffee. Like, just take it for granted that you're entitled to a coffee machine, you know, coffee line, espresso machine at work. But I think basically just having that mentality towards every bit of entitlement, stamping out entitlement and expecting people to accomplish things every day does compound over decades in his career.

What are you accomplishing this week? I like that it's a good frame because you're like, there's, there's got to be a sense of urgency, right? Most people just look at their life on a year, but they, they may, they might be sprinting for three to four months of that year instead of putting it more into, hey, what did you do this week? Let's try to get a month's worth of stuff done this week.

There's a principle, you know, I think of it as Max Levitune taught me. It's like chemistry. Like startups are like chemistry, engineering, psychology. Gas expands the size of the container. So if you give people a quarter, it'll take a quarter. If you tell people they have a month, it'll take a month. If you tell people it takes two weeks, it'll take two weeks. Tell them a week, it'll take a week. So you want to constantly compress the container size because that, those accomplishments, those building blocks add up over months, quarters, years, and now decades.

What about you personally? Because I, you know, I was talking to your chief of staff too, and he's like, you know what? Keith just has a guy for everything. Like, he, like anything he doesn't want to do. Like, every area of his life is systematized. There's a guy for this, that, that, like, it seems like you've kind of really tapped into the concept of leverage in a big way. Like, what are, what are your big time hacks that have allowed you to do so much?

Well, the most important thing is actually I lost another computer Thiel, which is people systematically undervalued their time. Like everybody has, as you point out, 24 hours in a day. And the more things you want to accomplish. And the more things you want to accomplish in parallel, the more you have to really be attuned to the value of time. So I basically try to focus my time on things that are super important to me and or to my goals and try to remove everything else and get leverage out of that. Now it's never perfect. Like I wish I could send someone to the doctor for me, you know, a dentist. Particularly if I could send a clone to the dentist. So you're never going to get 100%. But if you think about your calendar in a week, what fraction of that time is allocated to high leverage activities and what fractions drag coefficient. So if I can get it in the 80% is really effective. That's amazing. So I do tend to find ways to take the things either I'm not good at, not proficient at, or they're just not strategic and try to delegate them. Basically trade money for time if you can.

Do you audit your calendar?

I do all the time. Fortunately, my chief of staff, who you've talked with, works with my EA and they give me a report every quarter decomposed pretty precisely. So let's say X percent were new pitches with new founders, Y percent were bored. Meeting Z percent was like one on one meetings with founders, acts was kv, internal meetings, et cetera, et cetera. And then I look at the numbers, they compare it to prior quarters. And I do try to dial up or down if I see things that don't feel that strategic to me. So for example, I teach this to CEOs all the time. I'll give away the secret, but basically every time I meet with a new CEO, I say and they're somewhat frustrated by their time allocation and they're trying to get more out of their day or week or company. I basically ask them to go to a whiteboard, write out their three top priorities, and they write them out. And most CEOs are pretty proficient at identifying the top three priorities. Usually one's recruiting after they finish the exercise. I'm like, okay, now open your Google Calendar. And it's always a Google Calendar. And then let's see what fraction of time last week or last month actually maps to those priorities. And it's never 100%. There's often some discrepancies. And that actually shows the mismatch of time against the priorities is where you get get more success in matching them.

Yeah, that's a I need.

But a chief of staff is Jack's really good. So he definitely helps a lot.

So okay, yeah, so those Calendar audits are key. And just making sure that your priorities line up. You're looking at short term goals. Like, hey, what are we doing this week? Are our three most important activities. The majority of our work here. And then figuring out how to ruthlessly delegate everything else.

Let's. Let's give an illustration. So the classic example is almost every CEO says recruiting talent is my number one party.

Yeah.

I have almost never in 23 years found a CEO whose number one allocation of actual time is against recruiting.

Yes.

So by definition they're either lying to themselves or not effect not as effective as they could be.

So then you just kind of rework your calendar to reflect, hey I.

As close as possible. It's never going to be 100%.

Yeah.

Like there are things that you just kind of have to do, per my dentist example, and there's the business version of that. But you want to maximize the ratio.

The business dentist. Yes. The. You try to eliminate all the admin out of your.

Yeah, yeah, exactly.

I want to switch gears everyone. We, you know, we. I love this is so much great info on, on the startups and stuff, but there's, there's big macro things happening right now that I think are having a huge impact in the world in the future that are even bigger than business. You know, like the election coming up. There's just, there's so much going on here. You know, we're about, I think, four weeks out. A little bit less. A little bit less than four weeks out. But given the climate right now, the election around the corner, like what for you, what are the big kind of world events and political issues that you're most concerned about right now that you're thinking about?

Well, I think national security for the United States is threatened. I think the CCP is an existential threat to the way of life that Americans take for granted sometimes.

Yeah.

B, I think there's a lot of conflicts that could escalate if not handled properly between good and evil. And that's mostly in the Middle east at the moment. But I think those need to be managed very carefully and thoughtfully. And I think intellectually we're kind of in a bankrupt error in Washington right now. So I'd like to see that fixed. Obviously, I believe in success startups propelling the world into the future. And I think you want to encourage people both politically, socially, culturally to emulate success and not retard success. And I think we've been setting bad examples for. Or leadership in politics is sometimes set bad examples. So I'd like To embrace success. I think one of the best things about Miami, for example, is people here aspirationally want to be successful. They want their children to be successful. Regardless of what role you meet someone in, whether they're a barista, an Uber driver, a real estate professional, they all want to be successful. They want to be the best they can. They want their kids to have a better future. And I think we need to kind of rebuild America that way. That was how I was to going, was raised, born and raised. That's how I think society worked when I was growing up. And I think we sort of detoured from that and started criticizing, stigmatizing, and complaining and whining about successful people. So we need to fix that asap.

That's a good summary. I like that. So in light of that, where are you leaning on the political election and why?

Well, obviously I've supported Trump for president, which is gonna be the first time. I did not vote for him in 2016 or 20, but I think there's just no choice.

What changed for you then?

Well, I think 10, seven, you know, Hamas, basically proving that there's a lot of evil in the world and someone needs to confront it. I think it was unnecessary. I think if the administration in D.C. were different, that never would have happened. All my friends in Israel would be alive today. We would have not witnessed sort of the worst atrocities since the Holocaust. And I think we need to change. So I think that's number one. Secondly, I think the intellectual bankruptcy of the loft has become more stark. You can watch some old videos like the State of the Union or the DNC speech of Bill Clinton in 1992, and you would think it's like Donald Trump speaking, maybe even to the right of Donald Trump. So I think the left has just gone stir crazy, and so there isn't a choice from that side either.

Feels like the left went so far left that now if you're. If you were right, you're kind of in the middle there.

Well, I mean, like every, you know, Kamala Harris is the constellation of all the worst people in the world. She's importing. And the worst ideas, like, she's literally supported all the worst ideas over the last century. And so I just think it's like this, the easiest decision ever to support Trump, even though I was critical of him in 2016 and 20.

I think that's important to be able to change your mind too, in terms of new light, because I think a lot of people didn't support Trump at first.

I didn't support him in the primary. I, you know, obviously had a different candidate that I preferred, but I think there is good and evil, and he's on the right side.

He's on the right side. So if you could predict the future here for us, what do you think happens in the next four years if Kamala is elected?

Well, I don't think it'll happen, so I'm not too worried about it. I think there's a difference between. One distinction that I'll draw that hopefully transcends history because it's going to get taped and broadcast forever, is there's a difference between a close election and a volatile election. This election is not going to be close, but it is volatile. There are black swans in the world. The one most important lesson over the last five years of my life is how volatile the world can be. Like Covid, none of us had ever lived through anything like that, expected anything like that. There are things in the world that happen that just fundamentally shift everything called black swan events for a reason. So I think the election, still three weeks out, is subject to black swan events that are independent macro events, independent of any campaign. If no black swan occurs, Donald Trump will be the 47th president of the United States in a fairly significant landslide, at least from an electoral vote perspective.

Yeah, and I think there might be, like a gray swan, which is social media companies. Right. Like we saw in 2020, censorship of the Hunter Biden laptop story, which definitely swayed millions of votes. Mark Zuckerberg publicly admitted that they were censoring information.

Yep.

Facebook obviously controls the biggest demographic people in the world. Do you think that the social platforms are going to play a big role and potentially skew this this time?

Well, fortunately, X is a fairly open platform, and so it'd be much more difficult. There's just more transparency about attempting to censor information. I do think that that is true. You know, I saw JD Vance on TV yesterday talking about this. But the censorship of the Hunter Biden laptop, which proved that the CCP was funneling money to the Biden family, was both an accurate story by the New York Post and was completely censored on X. The Post account. The New York Post account was disabled. That is inconceivable to me that they shut down one of the most historically, you know, important publications in the history of the United States States for a true story, that's like, insane. And that did has impact. You know, somehow or another, Trump lost by somewhere between 44,000 77,000 votes, depending upon how you count. I do believe he lost on election day by 44,000 to 77,000 votes. But if the world knew that the CCP definitively was sending money to the Biden administration, I think it's easy to make up 50,000 votes just on that second thing. As my friend Delian tweeted about this morning, I also believe Pfizer withheld the COVID vaccine by three days intentionally to avoid Trump being reelected. I think there's lots of evidence of that. Obviously, they knew the vaccine was going to get approved more than three days before the election. If on that Sunday before the election, Pfizer announced, we have a vaccine for Covid, Trump easily wins reelection.

I'm curious because I fully resonate with your political points here. And, like, I believe this is a very easy, clear decision for the history of America, but there's a lot of really intelligent people in Silicon Valley that believe the diametric opposite of you and I. Cuban.

I mean, he's not very intelligent.

Yeah, yeah.

Nor is he in Silicon Valley. He just has an accomplishment.

He got a little bit lucky. But we'll say, like Reid Hoffman, Vinod. Yeah. They're smart guys.

Colleagues and actual colleagues of mine.

Actual colleagues of yours.

Reed and Vinod are very smart, very talented. Yeah.

So, like, what are they seeing? Like what?

Well, so in Vinod's case, I think he just personally sees the flaws of Donald Trump as a human. And putting aside whether he's right or wrong about that, it's a very valid perspective. You can critique humans. I actually think most people are supporting Trump as a protest against elite society censorship, and they see how vapid Kamala is. But it doesn't mean that Trump is, like, this perfect human being. So I think some of that is what he's tapping into and why he's tweeting. I think Regis has an incorrect worldview. He's had it forever. He's been, like, left since college. He just believes in socialism. At the end of the day, some versions of socialism. And psychologically, Vinod is not a socialist, he's a capitalist. He's been a very successful capitalist. He believes in capitalism and how capitalism can be channeled to improve society is his real goal in life. And I think he's very effective at it. I do think he's reacting to the personal traits, and, you know, it's hard to critique that. I just think there's other issues, too. Like, for example, like, what are we going to do about Iran? What are we going to do to support Israel? And you can have character flaws as a human but still be on the right side of that question, whereas I think the other choice is on the wrong side of every foreign policy question for the last 50 years.

Right. Even if that. Even. Let's just say Trump didn't have the most admirable qualities and you didn't support him as a person. If he's. If he was going to enact all the policies that were going to put America in the best position to be a great nation, we're gonna. We're gonna advocate for the policy and overlook some of the personal flaws.

It's a reasonable debate. Do you elect a president based upon personal traits or policy? You know, and it's probably a mix in most voters minds of both. Yeah. But I could easily see why someone would skew 9010 or I can justify screwing the other way. 90 10.

I think it's interesting too, that we, I think to get back to really, we continue to progress and maintain our status as a superpower and leading the world in technology, business, and everything else, we need more entrepreneurs in government, less lobbyists, less politicians. Like Elon wants to come in here to the government efficiency.

That'll be exciting. Very effective. I think we just need to alto people. And I think having had a role in the private sector certainly helps. So, for example, you know, Kamala. Neither Kamala nor Tim Wallace have ever had a private sector job in their entire life. I mean, maybe she worked at McDonald's, maybe she didn't, but that's the most experience she might have had in her entire life of earning a paycheck from real people.

Yeah.

And I think it's important to have that experience and build stuff. And it doesn't mean you have to do just that. You don't have to be a businessman for decades to be successful as a politician. But I think some experience where people voluntarily give you their money versus at the, you know, at gunpoint, they tax you and take your money, which is all her experience. And all his experience, I think, is not effective. Similarly, you know, I do believe that raising a family is important. And Donald Trump's raised a very successful family. I've had the benefit of meeting, you know, a lot of his family, and they're all great people, wonderful people, super excited. I'd be proud to have raised a family as well as he has, whereas, you know, Kamal has never raised a family. And I think that matters. You know, Deliana put this on steroids.

I would never invest in her.

Yeah, yeah, yeah. That I'm sure of. But. And you know, I admit there's five presidents in the history of the United States who didn't have children, but none in the last, as far as I can tell, in the last century or more. And so I think it's artifact of history. And, you know, three of the presidents were pretty good, two were very bad. So. But I think it is important if you're building a foundation for society and leading the Americans in the future, having raised children is a pretty important criteria, and having raised them well is an endorsement.

It's interesting, too, when you see Tim Waltz and his own family doesn't want to vote for him.

Yeah, well, of course. I mean, nobody, Nobody, anybody who knows him doesn't really want to vote for him. It's a little bit like Kamala, like, 93% of her staff quit. Imagine you were like working for an executive where 93%.

Imagine those glass door ratings.

No, no, no. Yeah, those are biased and distorted. I wouldn't do that. But just the stat of 93% of staff. And she's about to have more turnover this week, I'm pretty sure, because that campaign is in deep trouble at a.

At a high level. To what do you think the greatest threat to America right now is? Like, do you, like, there's looming talks of World War 3, Iran gaining more nuclear power, the tensions, the Middle East. We have Russia, the ccp.

Like, I don't think Russia will turn into, you know, an existential threat. Their economy isn't strong enough. Putin's pretty savvy and isn't going to do anything like crazy. Like, he's predictable in a certain sense.

I think Iran is the scariest.

Yeah. Iran is both crazy, unpredictable, and ideological in a. In a weird way. And, you know, enabling them to get nuclear power would be an unmitigated disaster. I think that is another critique of both Obama and Biden, that this was predictable and was preventable. And now it's going to take significant Israeli intervention to save us. This almost happened, you know, Syria almost got a nuclear weapon in the 1980s, and Israel bombed their nuclear factory, their nuclear sort of facilities in 1982 and three, I think. And that was critiqued by the world, but it actually saved the planet. And so I think one way or the other, we're going to have to destroy Iran's ability to get nuclear access. And the sooner the better. There's different ways to do it. You could bomb, you can sabotage. I mean, there are plenty of techniques. I'll leave that to the Mossad and my friend Mr. Netanyahu. But it's embarrassing that we've got this far.

Yeah. What's your take on the kind of political divide now on. On Israel? It seems like so many people are so quick to kind of turn their back now. And.

Well, it's interesting. I saw a poll, a rigorous poll from NBC News this morning.

Yeah.

And actually 88 of America supports Israel. Now, if you watch social media or you talk to elected Democratic officials, you get a different perspective. And certainly if you read, you know, CBS or something crazy or the New York Times.

Yeah.

All you do is read anti Semitic garbage. But like 88% of Americans notwithstanding that seem to understand there's a right and wrong in the Middle east. In Israel's, you know, a democracy. It's a very effective democracy. It's a very progressive democracy, actually, by any standard. Good news is normal Americans have a pretty good acid test, a pretty good barometer for truth.

And you think that under the Trump election, we have a strong relationship with Israel that.

Oh, absolutely. I saw, you know, the former ambassador to Israel commenting this morning. That and other people that I trust that have, you know, really understand Trump and understand Israel, that Trump would be the most supportive of Israel president we've had since at least Harry Truman, who recognized Israel, which was controversial in 1948. So I think that's absolutely the case. He moved the embassy to Jerusalem. He is a very strong supporter of Israel and he certainly understands the threat posed by Iran. He understands. He understood the threat back in administration one, when he was the 45th president, he sanctioned Iran. He basically bankrupted Iran. So they had no money. They had no money to support terrorists. Then by taking the sanctions off and allowing them to sell oil to the Chinese, 70% of their oil is actually sold to China. They developed $100 billion surplus, which they used to fund Hezbollah and Hamas, which is basically funding terrorism. It's insane to me that the Biden administration doesn't understand if you give bad people money, they're going to use it for bad purposes. It seems like the most obvious concept in the history of the world. And if you deprive them of money, they can't spend it. And, you know, terrorism takes money. Second thing is actually I believe that the missiles that were actually launched at Israel recently, a few weeks ago, were actually subject to sanctions under the Trump administration. And so Iran wouldn't have had those missiles. And then Biden, I believe, on the first day of office removed those sanctions. So he's also responsible for the missiles that are landing in Israel now because he was too naive about Iran or he had supporters. Actually, I Think he's both naive and Kamala is naive. But they also have people working for them that are, I don't know if they're officially spies, but they're certainly very sympathetic to the Irans, Iran people and the Iran administration. And I think they were sabotaging good ideas. Maybe not for the best reasons.

Yeah. Wow, that, that's a great synopsis too. And I think. Yeah. At the end of the day, personally for me, I like to think through about what is best for America, what's best for our well being. And I look at the national security is number one. Our economy, are we thriving? Are we?

Our economy is critical too. As you know, most Americans are not sitting in a luxury house in Miami and they're not in Silicon Valley. And inflation has really been extremely painful.

Yes.

In being able to afford groceries, housing, etc. And it was kind of unnecessary. This inflation was not required. When Trump left office, we were at 1.8% inflation, which is pretty good actually by historical standards. And I think by spending money artificially on stupid stuff, when the government prints money and spends money, it causes inflation, period. That's basic, basic, simple principle. I think we need to spend less government money, print less government money. I think there's ways to do that in curtail that and still provide for the national defense and other really important initiatives and possibly even lower taxes to lower the marginal tax rate. Yeah, but you need to be disciplined about it. Inflation penalizes the most poor people in the United States and the most middle class. Inflation doesn't affect me very much. I don't have like a loan on my house that, you know, is three times, four times more expensive than it used to be, et cetera. And so I think inflation is a tax on normal people. And it's, that's why normal people are voting with their feet. Like you saw also in the same NBC's, you know, poll I read yesterday, by a large margin, people prefer the economy under Trump than Biden. And when they were asked is their family better off under Trump, by a significant, significant margin, they said yes versus Biden. It's because they see the impact of inflation.

Yes.

And you know, inflation may be decelerating, but that just means the degree of difficulty is slowing down. It's not like prices are coming down. Prices are 20 to 80% higher. Even Obamacare, the premiums are 3x higher than when Trump left office. That means health care is basically unaffordable.

All fantastic frickin points. I could jam with you on this for another 45 minutes. I want to ask you a few, a few last personal questions. Right. Just at a high level, I'm curious, like if you had to create a recipe for, for what it means for you to live a world class life, what goes into living a world class life?

Well, Ben Franklin wrote the best pithy explanation ever, which I've sort of subscribed to since high school, which is you want to do something worth writing about or write something worth reading.

And that is the key, that's the key mantra. Life, a world class life. I love that.

Or do both. Like, or do as he did.

I think about, I'm like, I want to like live this incredible story and then I want to write it.

Yeah, you can do it. That order. You can write something worth reading like J.D. vance did. You could do the opposite order.

Yes, that's a good point actually. You know, people know you as an icon in Silicon Valley, right? Great, amazing investor, founder. We, we know, like the image of Keith Roboy. Right. But if you, if you were to take away all of your accomplishments, your accolades, the status you've built in Silicon Valley, like underneath all that, who is Keith Raboy?

You know, actually I think it's pretty similar. And I think that's, if you, you know, chat with people who know me, I think they'll say it's pretty authentic, but you're welcome to. I think that's what, you know, when people are like interviewing to like potentially work with me, I think that's the usual feedback they get is it's like pretty legit.

So how would you describe yourself then?

At the core of who you are, propelled by challenge. As we talked about, Motivated, disciplined, simple views, straightforward views, but just allow the discipline to kick in and it compounds. So as, you know, workout same time every day, don't miss. I think I missed seven workouts in five years, seven days. And that's including international travel across time zones. So. And I sleep like 8 hours most days or, you know, certainly leave the room to sleep for eight hours. I think like fundamentally success in life is just having the right habits and not deviating. And it's like anything else. No one's gonna be 100%, but you wanna be as close to 99% as you can. And they just kick in. So I try to do the same things all the time. I eat blueberries every day. That's what we're joking about. Same food, same workouts, same sleep. And maximize your potential and then find challenges that propel you. I generally have a philosophy that if you're not growing, you're retarding. And so I always looking, I'm always looking for new challenges, harder, more difficult things because I think you do age and decay if you're not exercising muscles. So think about bodybuilding. Works that way. Professional aspirations, work that way. Family aspirations. You want to challenge yourself all the time. So you may know for fun occasionally. I teach a berries class that was terrifying for me initially. The reason why I did it was it was a challenge like being on stage being awesome at a field that I don't know much about, you know, in terms of expertise was a challenge and embraced it. And I was nervous. And actually that's a sign. The more nervous you get about something, the more you know it's your body reacting. Nerve is a body reaction to challenging yourself. So if something feels comfortable, it's too easy and stop doing it and find something that makes you want to throw up, that you feel that. Oh my God, this is so difficult. Basketball players have this, you know, feeling all the time. Bill Russell used to throw up in the locker room before playoff games. This happens all the time. When you know you're at the cutting edge of what you can do, your body reacts with certain kinds of emotions. And if you don't feel that, you know, that it's too easy and complaint, you don't. Complacency kills basically.

It seems like underneath it all you're just driven by this innate curiosity to see how far you can go.

Intellectual curiosity. And adrenaline.

And adrenaline.

I need an adrenaline rush. So they, you know, it's one of the challenges of being a VC is there's not a lot of now natural adrenaline adventure because feedback cycles are so long that the adrenaline kind of dissipates. So one of the reasons why I start companies every so often, every call, five years as a VC is I need more adrenaline.

That makes a lot of sense now I got a better window into you, I think. You know, as a last question here, it's interesting because when you see great people, I think the greater the person, the greater the individuals behind them. Right? They were just surrounded by a lot of people that made them look really good too. That help propel them. I'm curious for you who, who is one person that's had like an asymmetric impact on your success in life?

Well, I agree philosophically, like there's this old adage that you are, you know, the average of the five people you spend the most time with and I think being disciplined and thoughtful about who do you spend the most time with and why? Because you are going to, for better or worse, pick up traits.

Yes.

Subtly or otherwise. And so I think that's, that's the first, most important lesson is people could map their calendar again. Who do you spend the most time with and what are the characteristics of those five people? And are those people I want to emulate or there's people there for compelling me to grow, or are they retarding me or slowing me down, or am I picking up negative traits? And I think a lot of people are not as conscious as they should be. But in my history, I learned a lot about building a technology company, philosophically, conceptually, from Peter Thiel. I learned a lot about venture and building companies from a venture board perspective from Vanode. I think they've been incredible ingredients. And I'm always remixing. It's sort of like being a dj. Peter has his tracks, Vanode's got his tracks, and I'm remixing them. And when I'm lucky, the remix is better than the original. And just like in the real world, often the original is pretty good. But I can name some remixes that I prefer over the original song. Like I have a remix. I have an Alessia remix of a Chainsmoker song. I have a Glandis remix of a Kygo song that actually are superior to the original. So once in a while I take a Peter idea, remix it, and it's better. Once in a while I'll take the idea, remix it, and hopefully it's better.

I like that, man. Let's pretend this, you know, this many, many years from now, this is kind of your last day on earth, and you get to, you get to leave the world with a message, a heartfelt message you want to leave the world with. What do you want to tell them?

I think being conscious about are you growing or are you retarding? Are you challenging yourself or are you slowing down? And if you embrace that philosophy, you'll think about every day, every hour, through a different lens. And what am I doing to grow today? What am I doing to challenge myself this hour, this day, this minute? I think there's different challenges. It doesn't mean my version of a challenge, which may be building a tech company, or my version of a challenge may be propelling some candidate, or my version of a challenge may be to have the lowest resting heart rate or, you know, two minute recovery or some athletic thing. But what is your challenge? And then how do you force yourself, compel yourself to constantly challenge yourself to do better, faster, more, and then if not, you're going to slow down and you're going to regress. Like body's emotions stay in motion and they either go, they're either in motion positively or negatively. They're not static.

It's never static. It's always moving. I, I think what I took away from this interview I wanted. I always just want to run through a wall if I talk to you. But I like the idea of constantly pursuing a very big, meaty, challenging thing that scares you, makes you want to throw up. Like if you don't have that in your life, go find that and, and figure that out quickly. Otherwise you're kind of just, you're existing, but you're not fully living.

Yeah. This path of least resistance, a bit of, you know, in the unfortunate thing is the more success you have, the tendency kicks in even more so. So the more success, the more that you're on some path, glide path, the easier it is to just stay on the glide path. So it's actually more important, the more success you have to reinvent yourself, to rethink yourself, to re challenge yourself, or you definitely will get off that glide.

Path, which is what you do too. Because money in and of itself can't be a big motivator for you anymore.

No.

It probably doesn't get you that excited.

It doesn't. And I think it's not a poor motivator generally. Well, you know, maybe some threshold, you know, is useful, but like after that, I don't think it's particular. I do know people who are, per your point, our point or discussion about people have their own motivations. I do know some people who are motivated by it and it works for them. But I don't think it would work for me and I don't think it would work for many, many people. So I think having a different intrinsic motivation is probably more likely to succeed and work empower people more often than the few people I know that actually money does work as a score, sort of their own scoreboard. I think fundamentally it does come down to what do you want to accomplish. And accomplishments vary, but you should accomplish something.

I love it, man. Thanks for coming on again.

Pleasure to be with you.